Studies are proposed to execute the total synthesis of several cyclopentanoid sesquiterpenes utilizing a new [2+2] photocycloaddition-cyclobutane fragmentation sequence. The substrates to be used in the photocycloaddition reactions will be prepared by a conjugate addition-ring closure sequence of acetylenic diesters. Pentalenolactone, a lypophilic antibiotic, and its proposed biosynthetic precursors pentalenic acid and pentalenolactones E, G, and H will be prepared through this method. A synthesis of the antileukemic agent, quadrone, will also be undertaken.